Technology Process of 1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselanyl-4-thio-β-D-pentofuranosyl]uracil
There total 11 articles about 1-[(1R,2R,4S)-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-fluoro-2-phenylselanyl-4-thio-β-D-pentofuranosyl]uracil which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 94 percent / H2 / 5 percent Pd/C / ethyl acetate / 3 h
2.1: NaOH / ethanol; H2O / 2 h / 20 °C
2.2: dimethylsulfoxide / 1 h
3.1: 7.52 g / I2; imidazole; PPh3 / toluene / 4 h / 60 °C
4.1: 87 percent / dimethylformamide / 8 h / 20 °C
5.1: DIBAL-H / toluene; hexane / 1 h / -78 °C
6.1: Ac2O; DMSO / 24 h / 20 °C
7.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C
7.2: TMSCl / tetrahydrofuran / -78 - 20 °C
7.3: 72 percent / tetrahydrofuran / 1 h / -78 °C
8.1: DIBAL-H / hexane; toluene / 1 h / -78 °C
9.1: TEA; DMAP / CH2Cl2 / 3 h / 20 °C
10.1: TMSOTf / acetonitrile
With
1H-imidazole; dmap; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; TEA; hydrogen; iodine; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; triphenylphosphine; lithium hexamethyldisilazane;
5 percent Pd/C;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
6.1: Moffat-type oxidation;
DOI:10.1021/jm020246+
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C
1.2: TMSCl / tetrahydrofuran / -78 - 20 °C
1.3: 72 percent / tetrahydrofuran / 1 h / -78 °C
2.1: DIBAL-H / hexane; toluene / 1 h / -78 °C
3.1: TEA; DMAP / CH2Cl2 / 3 h / 20 °C
4.1: TMSOTf / acetonitrile
With
dmap; trimethylsilyl trifluoromethanesulfonate; TEA; diisobutylaluminium hydride; lithium hexamethyldisilazane;
In
tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jm020246+
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: Ac2O; DMSO / 24 h / 20 °C
2.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C
2.2: TMSCl / tetrahydrofuran / -78 - 20 °C
2.3: 72 percent / tetrahydrofuran / 1 h / -78 °C
3.1: DIBAL-H / hexane; toluene / 1 h / -78 °C
4.1: TEA; DMAP / CH2Cl2 / 3 h / 20 °C
5.1: TMSOTf / acetonitrile
With
dmap; trimethylsilyl trifluoromethanesulfonate; TEA; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile;
1.1: Moffat-type oxidation;
DOI:10.1021/jm020246+
